Imidazole → Methyl (2S)-2-[(tert-butyldimethylsilyl)oxy]propanoate

Participants

Reaction Steps

To a solution of (S)-methyl 2-hydroxypropanoate (1.00 g, 9.61 mmol) in DMF (10 mL) at rt, were added imidazole (0.981 g, 14.41 mmol) and TBS-Cl (1.737 g, 11.53 mmol). The mixture was stirred at rt for 3 h. The reaction mixture was diluted with hexanes. The organic phase was washed with water (2×) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 10% ethyl acetate/hexanes) to give 17A (1.73 g, 7.92 mmol, 82% yield) as a colorless oil. 1H NMR (400 MHz, chloroform-d) δ ppm 4.34 (q, J=6.7 Hz, 1H) 3.72 (s, 3H) 1.40 (d, J=6.8 Hz, 3H) 0.90 (s, 8H) 0.09 (d, J=10.8 Hz, 6H).

Provenance & Evidence